$227 Cheap Flights from Kailua-Kona (KOA) to Chicago (MDW)

View $227 flight on Fri, Feb 27, 2026Opens in a new window

Popular airlines from Kona Intl. Airport (KOA) to Chicago Midway Airport (MDW)

Cheap Flights from Kailua-Kona to Chicago (KOA-MDW)

Prices were available within the past 7 days and start at $227 for one-way flights and $493 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Mar 10 - Tue, Mar 24
KOA
Kona Coast
MDW
Chicago
$493 Roundtrip, found 21 hours ago
$493
Roundtrip
found 21 hours ago
Select Delta flight, departing Tue, Mar 10 from Kona Coast to Chicago, returning Tue, Mar 24, priced at $493 found 21 hours ago
Southwest Airlines
Tue, Feb 10 - Tue, Feb 17
KOA
Kona Coast
MDW
Chicago
$530 Roundtrip, found 4 days ago
$530
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Tue, Feb 10 from Kona Coast to Chicago, returning Tue, Feb 17, priced at $530 found 4 days ago
Southwest Airlines
Wed, Dec 24 - Wed, Jan 7
KOA
Kona Coast
MDW
Chicago
$547 Roundtrip, found 5 days ago
$547
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Dec 24 from Kona Coast to Chicago, returning Wed, Jan 7, priced at $547 found 5 days ago
Southwest Airlines
Wed, Dec 24 - Wed, Jan 7
KOA
Kona Coast
MDW
Chicago
$553 Roundtrip, found 5 days ago
$553
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Dec 24 from Kona Coast to Chicago, returning Wed, Jan 7, priced at $553 found 5 days ago
Southwest Airlines
Wed, Dec 10 - Mon, Dec 15
KOA
Kona Coast
MDW
Chicago
$578 Roundtrip, found 5 days ago
$578
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Dec 10 from Kona Coast to Chicago, returning Mon, Dec 15, priced at $578 found 5 days ago
Southwest Airlines
Tue, Dec 16 - Fri, Jan 9
KOA
Kona Coast
MDW
Chicago
$578 Roundtrip, found 3 days ago
$578
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Dec 16 from Kona Coast to Chicago, returning Fri, Jan 9, priced at $578 found 3 days ago
Southwest Airlines
Mon, Dec 15 - Mon, Jan 5
KOA
Kona Coast
MDW
Chicago
$580 Roundtrip, found 3 days ago
$580
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Mon, Dec 15 from Kona Coast to Chicago, returning Mon, Jan 5, priced at $580 found 3 days ago
Southwest Airlines
Tue, Feb 10 - Tue, Feb 17
KOA
Kona Coast
MDW
Chicago
$583 Roundtrip, found 4 days ago
$583
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Tue, Feb 10 from Kona Coast to Chicago, returning Tue, Feb 17, priced at $583 found 4 days ago
Southwest Airlines
Mon, Dec 15 - Mon, Jan 5
KOA
Kona Coast
MDW
Chicago
$586 Roundtrip, found 3 days ago
$586
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Mon, Dec 15 from Kona Coast to Chicago, returning Mon, Jan 5, priced at $586 found 3 days ago
Delta
Fri, Dec 5 - Mon, Dec 8
KOA
Kona Coast
MDW
Chicago
$587 Roundtrip, found 2 hours ago
$587
Roundtrip
found 2 hours ago
Select Delta flight, departing Fri, Dec 5 from Kona Coast to Chicago, returning Mon, Dec 8, priced at $587 found 2 hours ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $663
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $663

Frequently asked questions

How much does a flight from Kona Intl. Airport (KOA) to Midway Intl. Airport (MDW) cost?
Grab a cheap one-way flight from $227 or cheap return flight from $493 from Kona Intl. Airport (KOA) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Kona Intl. Airport (KOA) to Midway Intl. Airport (MDW)?
Planning your getaway for March may help you find better deals, as it's the cheapest month for flights between KOA and MDW. You'll usually find the lowest fares during the off-season.
What is the cheapest airline that flies from Kona Intl. Airport (KOA) to Midway Intl. Airport (MDW)?
To find the cheapest airline flying from KOA to MDW, use Expedia's filter tool. Customize your search based on what matters most to you, such as preferred carriers and cabin class. You can then sort your results by "Price (lowest to highest)" to list the most affordable options first.
How many flights per day from Kona Intl. Airport (KOA) to Midway Intl. Airport (MDW)?
Direct flights from Kona Intl. Airport (KOA) to Midway Intl. Airport (MDW) aren't available daily, so you'll have to take a flight with a layover. Explore your options with our filter tool. Enter your dates and click on either "1 Stop" or "2+ Stops."
What day of the week has the most flights from KOA to MDW?
You'll typically find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can vary from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Kona Intl. Airport (KOA) to Midway Intl. Airport (MDW)?
To arrive at Midway Intl. Airport (MDW) on time, opt for a flight that takes off from Kona Intl. Airport (KOA) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Kona Intl. Airport (KOA)?
O'Hare Intl. Airport (ORD) is the only airport in Chicago with direct flights from Kona Intl. Airport (KOA). Explore your options and find affordable fares on Expedia.
Is it cheaper to buy a plane ticket from Kona Intl. Airport (KOA) to Midway Intl. Airport (MDW) last-minute?
Booking your plane ticket from KOA to MDW right before your getaway is usually more expensive. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a KOA to MDW flight and hotel package?
Opting for a KOA to MDW flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip in one place. Select from our impressive range of accommodations and then add activities, car rentals and flights to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Kona Intl. Airport (KOA) to Midway Intl. Airport (MDW)?
If you reserved your KOA to MDW flight within the last 24 hours, you may be able to modify or cancel it at no cost. Depending on the airline and the fare type you purchased, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal if you'd like more information.

Travel information

Origin airport
Kona Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$493
Distance
4215 mi

Book with confidence

Kailua-Kona to Chicago Flights

The cheapest times to fly from Kailua-Kona to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Kailua-Kona to Chicago are during the month of March. You can find some of the cheapest flights from Kailua-Kona to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Kailua-Kona to Chicago

Sunday is one of the best days to book for cheap flights from Kailua-Kona to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Kailua-Kona to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Kailua-Kona to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $227 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Kailua-Kona to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Kailua-Kona to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Kailua-Kona to Chicago Flights

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*Available to One Key members.